Be My Valentine
by MoonlightShadow1998
Summary: It's Valentine's Day, and Karen wants to finally ask Grace out on a date.


"So, any plans for tomorrow? Are you finally gonna ask her out?"

Karen almost choked on her Martini. "What? Who?" She was shocked at Jack's questions, but she tried her best to hide it. "I don't know what you're talking about!"

"I'm talking about Grace of course!" He sat down next to her. "I know you like her. A lot." Jack looked at her with a huge grin over his face, and she knew he got her. But she wasn't going to give up easily.

"Oh, come on Jackie, don't be ridiculous. Grace is a friend, but there is nothing more between us. I mean, you've seen the way she dresses, right?" She looked around the room nervously, trying to avoid Jack's gaze. Then she downed the rest of her Martini.

"You can't fool me, Kare. I've noticed the way you look at her. _That_ is definitely not just friendship." He knew Karen didn't like to talk about feelings, but she _had _to. He couldn't stand seeing her be heartbroken over Grace anymore. And tomorrow was the perfect day to change that. It was Valentine's Day after all.

"So what if you're right?" She spoke so quietly that he almost couldn't hear her voice, and she didn't even manage to look up from the empty glass in her hand.

"Having feelings is not a bad thing, Karen. I know you don't like them, but you can't ignore them forever. And tomorrow is Valentine's Day. It's, like, the _perfect_ day to finally ask her out."

"And what if she says no? As far as I know she's not even into women. Why should she want to go on a date with me?"

Jack reached out and grabbed Karen's hand. "Because you are an amazing person, and you mean a lot to Grace. She will be really happy to spend the evening with you. Come on, where is the Karen I know? I've never seen you this insecure before, and I don't like that. _I_ am the one whose supposed to be insecure and doubt everything I do, and you're supposed to tell me how awesome I am. Not the other way round." That managed to make her smile, and she finally looked up from her glass.

"Alright, poodle, what is your plan? What should I do to ask her? She's really important to me, and I want this to be special."

"Don't worry, I have a plan."

When Grace came into the office the next morning something was weird. Not because it was Valentine's Day, that's just a day like all the others (right?). The weird thing was that Karen was already there.

"Karen, what are you doing here? It's not even 9.30 yet."

"Oh, hi, Gracie. I just thought I'd come in early once in eight years."

"Well, technically you're not early, because originally you were supposed to start working at 8, every day, but you never did. So, really, you're just earlier than usual. Which doesn't mean I don't appreciate it." She looked at her assistant to try and reassure her how happy she was about it, and to maybe encourage her to come to work earlier more often. Still, Grace was really suspicious about why Karen would be there early, but she was distracted by an enormous bouquet of flowers standing on top of her design table before she could dive into it further.

"Wow, these are beautiful!" She went up to the bouquet to take a closer look. It was a colorful yet classy arrangement of red, violet and pink tulips, about 50 of them. Hidden between the flowers was a card. She took it out, careful not to damage any of the tulips, then she opened it and read out loud:

"_Angels we have heard on high_

_Sing about her beauty, her flaming red hair,_

_Her smile, that can be seen from space_

_Angels, there up in the sky_

_Praise her humor and smarts everywhere_

_Perfection, thy name is Grace._

_To the most incredible woman I've ever met_

_Will you be my Valentine?"_

She looked up from the card. "I think I've never read something so beautiful in my life." She turned the card around to see who send them, only to find that it wasn't signed. "Karen, do you have any idea who send them? There is no name on the card. Did the delivery man maybe say something about it?"

"No, he didn't. But I still know who send them."

"Really? Who was it?" She was really excited to know. Someone who wrote a card like this, and sent her her favorite flowers must be someone special.

"I did."

Grace couldn't believe what she had just heard. Karen sent her those flowers? Karen, who sometimes had trouble remembering Grace's _name_ correctly.

"You?" She couldn't do anything but stare at her assistant in shock.

The moment she saw Grace's reaction Karen knew it was wrong to ask her out. But now it was too late, and all she could do was try to save her friendship with Grace, and hope they both could just forget about it.

"Grace, I'm so sorry. I knew I should have never listened to Jack..." She turned away from the red-haired woman, and let her head sink down. "Can we just forget about it, and still be friends?"

"No."

Karen swallowed hard. She had just lost her best friend, and she had no idea how she could fix this. _If_ there was a way to fix it.

"No, I don't want to forget it. And I would love to be your Valentine."

These words made her assistant turn around quickly and she looked at her, eyes wide opened.

"Are- Are you being serious?" She barely managed to speak, because she was so nervous.

"Yes, I am. I would love to be your Valentine, and I would love to spend the day with you." She smiled brightly, and she could see Karen's face lighting up just the same.

"So, I was thinking I could take you out to dinner, to this new Italian Restaurant, Francesco's. I could get us the best table, Francesco still owes me one for going on a date with his brother." She twisted her mouth in disgust thinking back to that horrible evening. "What do you say?"

"Yes, that sounds perfect. So, when do we meet? Cause I will need some time to change and get ready."

"Well, how about I pick you up at seven?"

"Sounds good, it means I still have enough time to get some work done today." She smiled and sniffed at the tulips. This was going to be a great evening.

"Oh, Jackie, I'm so nervous!"

"You don't have to be, Kare. This evening is going to be fabulous."

"I still can't believe she actually said yes. What do you think about this one?" She held up a a red velvet dress, and looked at herself in the mirror.

"Definitely not. I knew she would say yes, I mean, who would say no to a date with _you_?"

She smiled at Jack, and threw the dress on top of the pile that had built up. They had been searching for _the_ dress for almost an hour, and by now half of her wardrobe was lying on the ground.

"What if this evening doesn't go well? She is my best friend-", Jack looked at her confusedly, "-sorry, my best _female _friend, and I'm afraid I will lose her."

"You won't lose her Karen. She wouldn't have agreed to the date if she didn't feel something for you. Oh, what about that?" He stood up and grabbed a black, knee length, off-shoulder dress off the rack. "That looks perfect."

"You think?" She took the dress out of his hand, and held it up in front of her. "Well, I guess it would be a good choice."

"Better than good. I think we finally found the dress. Come on, put it on, I wanna see it, I wanna see it!" He was jumping up and down, and clapping his hands like a seal.

"Alright. We still have a lot to do, and I have to pick Gracie up in-", she took a look at her watch, "-about one and a half hours. We have to hurry a little."

"Don't worry, we got this."

"Hey Grace, you're home early."

"I don't have time to talk, Will, I gotta get changed, I have a date." She rushed past him and into her room.

"Sitting alone in front of the television, watching Bridget Jones and eating pizza and ice cream while crying is not a date. You know that, right?"

"Funny as always, Will." She really had better things to do than argue with him. There was only an hour left until Karen was going to pick her up, and she didn't have the slightest idea what to wear yet. "I'm talking about a real date."

"Oh, wow, so who's the lucky guy?"

"It's not a guy", she started sorting through her clothes, searching for the perfect outfit to wear, "it's Karen."

"_Karen?_ Dark hair, filthy rich, always drunk, your assistant Karen?"

"Yeah, what other Karens do you know?"

"None, I'm just confused. Why are you going on a date with Karen?"

"Because she asked me out." She pulled a black sequined dress out of her closet, and started changing.

"I figured that. What I mean is, why did you say yes? You're not even into women."

She came out of her room, wanting Will's opinion on her outfit.

"Not women in general, but Karen – she is special. You know, I always felt something when we kissed. So I thought, why not say yes and see what happens? It's Valentine's Day after all. What do you think of the dress?"

"It's great, if you're going to a costume party. As a disco ball. Where is she taking you anyways?"

"She said she could get us a table at this new Italian place, Francesco's. She knows the owner or something."

"You're going to Francesco's? Oh, Grace, you _definitely _need my help with your outfit. They wouldn't even let you within 50 feet of the restaurant looking like this. Do you know how fancy this place is?" He ushered her back into her room.

"Alright, let's see what you have in here." He started looking through her closet, trying to find something to make her look presentable. "So what do you mean she's special and you felt something when you kissed? What _did_ you feel?"

"I don't know. It was a tickling, but it wasn't uncomfortable. It felt pretty great, actually. I would have never acted on it, cause I didn't think that maybe there was something on her side too. But since she asked me out, I thought this is my chance. And if the evening doesn't go well we can still be friends."

"You really think that?" He looked at her, worried.

"Well, yeah. Nothing has changed between us. Not really."

"Ok, we will see. And _I_ see the perfect dress for you." He pulled a dark green, floor length dress out of the depths of her closet. "Why have I never seen you wear this? It's gorgeous. And it goes amazingly well with your hair."

"I bought that years ago. Forgot I even had it."

"Then let's try it on."

She slipped out of the black dress, and into the green one.

"Now that looks like an outfit you'd actually want to be seen in. We just have to find the right shoes- oh, how about these?" He pulled out a pair of simple black heels, and handed them to Grace to put on. "What time are you meeting?"

"She said she will pick me up at seven, so we have about 45 minutes left."

"Great, so we still have enough time to do something about your hair."

"What's wrong with my hair?" She grabbed her locks and started stroking them.

"It's fine, for a day at the office. But you don't want Karen to criticize you again, do you?"

She shook her head quickly.

"Then we should get started."

Will managed to make her hair look less messy, and tamed her locks a little (and fixated it with a whole bottle of hairspray; how she would get that out the next day wasn't his problem) and Grace put on a little makeup to match her newfound style. She got ready just in time for Karen to knock on the door.

She had been feeling fine before, but now she was starting to get a little panicky, so she looked to Will for help.

"Just breathe, Grace, everything will be fine."

She did as told and then proceeded to open the door.

"Hey Karen. Wow, you look amazing." Grace couldn't take her eyes off her assistant. She was always gorgeous, without a doubt, but tonight she looked especially beautiful.

"I know, honey." Still, Karen couldn't help but blush a little at Grace's compliment. "You look beautiful too. Thank you, Will." She looked past Grace and gave a little nod to Will, who was sitting at the kitchen table.

"Why are you thanking Will? Don't you think I could pull this off on my own?" Grace gestured up and down her own body.

"Gracie, we both know the way you dress. If you picked out your outfit, you'd probably wear a dark-grey sequined dress and definitely not those shoes. Right?" She looked at her with pity and smiled a little.

"It was black", muttered Grace under her breath. "But I don't want to argue with you, Kare. Not tonight. Shall we?"

"Let's go." Karen held out her arm and Grace took her hand. She waved back at Will with the other one. "Don't wait for me."

Karen didn't lie when she said she could get them the best table. They had an amazing view out the window on Hudson River, and the restaurant had a romantic atmosphere, with candles and flowers. When they sat down, Karen ordered a fancy bottle of red wine and they started to look at their menus.

"You know, I was really surprised when you asked me out. But I'm glad you did." Grace looked up and smiled at Karen.

"I'm glad you said yes."

"You thought I would turn you down?"

"I wasn't sure. I thought it might be, you know, weird." Karen looked a little embarrassed, and quickly turned her sight back to her menu.

"Why would it be weird?"

"Well, because we are working together, and we're friends." She stopped for a second, and when she continued, her voice was barely audible. "And because I'm a woman."

"That's true, but you are special. And there is no person in the world I'd rather be here with than you." Karen looked back up at Grace, with a big smile on her face. "So let's enjoy our date, and see where the evening goes."

"That sounds good, honey."

Karen insisted on accompanying Grace up to her apartment door, and Grace wasn't mad about it. They spent the whole evening talking and laughing, and it was well after 11 when they finally left the restaurant.

"It was a wonderful evening, Gracie. Thank you for going on this date with me." Karen looked at Grace shyly, but with a smile on her lips.

"I have to thank you. That was the most amazing evening I've had in a long time." She took a step towards Karen and put her hand on her cheek. Then she closed the distance between their faces, putting her lips on the dark-haired woman's and kissing her, slowly at first, but it soon turned more passionate. When they finally pulled away from each other neither of them could breathe properly.

"You know, this evening doesn't have to be over yet. Do you want to come in?" Karen just nodded in agreement.

"I was hoping you'd say yes." Grace smiled at Karen, and then pulled her into another passionate kiss.


End file.
